Louisville’s Urban Bourbon Trail Doesn’t Have To Be a Liver Challenge

A Manhattan cocktail at Sway on the Urban Bourbon Trail in Louisville, Kentucky (photo by Sheila Scarborough)

To preserve the health of your liver, it’s important to know that to win your prize Trail t-shirt from the Louisville, Kentucky Visitor Center, you do not need to order bourbon (or any alcohol at all) at each of the six stops you choose on Louisville’s Urban Bourbon Trail.

Since I was attending and speaking at a tourism conference in town, it did not seem like a good idea to be slamming back bourbon in between breakout sessions. Still, to work in six bar visits in about three days took some planning. I wish we’d had time to also learn how bourbon barrels are made, which is another cool thing to do near Louisville.

Pick up one of the passports in any of the 30 establishments on the Trail, or at the Visitor Center, and get moving quickly. Try to pick “two-fer” places where you can get a stamp while you’re eating a meal. There’s a map in the passport and one online.

Each bar on the Trail has a signature cocktail, and during our stop at Sway we met the actual bartender who created their drink – a “Bourbon Berry” that included strawberry, mint, and ginger. My conference companion Sarah let me sip hers, and it was delicious!

At one point we ended up under a freeway overpass, but not because we were loaded….

My conference friend Sarah trolling for selfies at the Troll Pub under a freeway bridge on the Urban Bourbon Trail in Louisville KY (photo by Sheila Scarborough)

The Troll Pub Under the Bridge pub is a little tricky to find, but worth the trek. It’s in a basement and when you walk in, it feels super-cozy and welcoming.

It was late when we finally made it to the Troll, after a detour to a place called Jockey Silks Bourbon Bar that seems to have rather irregular hours and was closed when we visited.

On our last day at the conference, we did have to sneak out during one open session to hit our last place, Proof, inside the 21c Hotel Louisville, which like all 21c properties has an art museum and gallery in the lobby that’s open to anyone.

Urban Bourbon Trail cocktail at Proof on Main in the 21c Hotel downtown Louisville, KY. You can see my black ink stamp from there on the lower left side – they’re different for every bar. (photo by Sheila Scarborough)

Many of the bars are within walking distance of each other around downtown Louisville, but when timing was tight we just grabbed a Lyft to get us back and forth faster.

Another tip – make one of your stops the historic Brown Hotel, so you can try the famous Hot Brown open-faced sandwich AND get your bar stamp from their lobby bar or in-restaurant bar.

A Hot Brown at the Brown Hotel in Louisville KY (photo by Sheila Scarborough)

There are other versions of the Hot Brown around town – here’s the Hot Brown Hop trail if you want to sample – but the one at the Brown Hotel is the original creation from the 1920s. Get the smaller version; it is very rich and filling.

Speaking of food, here’s what I spotted during a stop at the Evan Williams distillery (not a stop on the Trail, but still a worthy diversion)….

To be honest, I thought the design was a little lame. The words are jammed into some sort of barrel outline, which makes it confusing to read. There’s a small Urban Bourbon Trail logo on the back of the shirt, but whatever this barrel is doesn’t really shout, “I drank a lot of bourbon in Louisville and you can, too!”

Then again, maybe that’s not something I need to be telling the world. We’ll keep it our secret, okay?

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